Research on emotional labor has shown that workers who are required to feign emotions are more likely to suffer ill effects than those who are able to deep act their emotions. The authors argue that what may stand between surface and deep acting is workers’ ability to claim the kind of socially valued role that makes their enactment of emotional display rules seem consistent with that role. The authors draw on observations and interviews with workers in the debt settlement industry to show that men who were agents were able to claim that they were educating clients rather than selling to them. This made it possible for them to avoid feeling that they were taking advantage of customers who might have been better off without the service they sold them. Men were able to help clients in a way that did not conflict with their role as salespeople. Women agents, by contrast, were not able to style themselves educators. Instead, clients and employers expected them to adopt a therapeutic role with their clients. However, this role conflicted sharply with the expectation that agents be effective salespeople and forced women agents to feign feelings of care and optimism. Clients, coworkers, and employers, the authors show, shaped workers’ freedom to define their emotional labor in satisfying ways.